From the Ashram to San Sebastián to a villa outside Florence, our city’s wanderers are taking the notion of holidaying to new heights.

Mykonos

Brian BolkeOwner, Forty Five TenDestination: Mykonos.In Residence: We are staying at the Belvedere, where we’ve stayed the last few years. It’s the perfect location in the middle of town.Raison d’être: Mykonos is our favorite place to really escape. In August, when we go, much of Europe is on holiday, so it feels even more like you are on vacation. Everyone is in such a good mood.Posse: My husband, Faisal Halum.First Things First: We rent four-wheelers and head straight to Nammos beach club. Possibly the sexiest place on the planet. You lie in the sun for a few hours — the people-watching is crazy — in front of the yachts in the bay until lunch (lobster pasta), which starts about 3:30 pm. People literally start dancing on the tables at 4:30 pm with jeroboams of Whispering Angel rosé, then it ends at six, when everyone retreats to their hotels to nap until they go out again to dinner about 11 pm.

Auckland

Chris ByrneCo-founder, Dallas Art FairDestination: Auckland in May, Sainte-Maxime in July, and East Hampton in August.In Residence: My house in East Hampton, and I’ll be staying with friends in Sainte-Maxime.Raison d’etre: I work with New Zealand artist Susan Te Kahurangi King and will be in Auckland preparing for her upcoming exhibition at the Institute of Contemporary Art, Miami. In August, Dallas Contemporary will host a cocktail party for Bruce Weber at my East Hampton house, and we also look forward to welcoming Jerry the Marble Faun (from the documentary Grey Gardens) during his residency at the studio. The East Hampton house and studio was owned by Elaine de Kooning; her biographer Cathy Curtis is also planning to visit.Posse: In Auckland, Tina Kukielski (executive director of ART21), who is curating Susan Te Kahurangi King’s first museum exhibition. In Sainte-Maxime, I’ll stay with friends Caroline and Max Tilliette.First Things First: A run on the beach.

Los Cabos

Brooke HortenstineCo-founder, Ashlar Projects; contributing editor, PaperCityDestination: Cabo San Lucas.Residence: We are staying at Casa Edwards, a beachfront compound in the Bahia Rocas of Palmilla.Raison d’être: We wish for a recess on the beach, and Casa Edwards will grant it. The house is staffed by Juan Ramon (who can make anything happen), is on the beach steps away from the One&Only Palmilla resort, has eight bedrooms (all with ocean views), and if you simply can’t have one more scoop of fresh guacamole poolside, then Flora Farm, The Office and Edith’s are all excellent foodie excursions.Posse: Kristin Gray, birthday girl Missy Wyszynski, Jenny Moss, Jamie Jo Hayes, Dawn Greiner and several more girlfriends.First Things First: We’ll don bathing suits and order up poolside margaritas made with Siete Leguas Tequila Blanco, fresh lime juice and a drop of agave nectar.

Lake Como

Jan ShowersInterior designerDestinations: Jim [Showers] and I are going to Harbour Island in June to celebrate two big birthdays: Jim’s and our daughter Susanna’s. Jim and I will be on Lake Como for a month — we travel to Switzerland while there and spend a few days in Milan. When we get back, end of August, we go to Telluride for the film festival the first week in September.In Residence: We rent the same villa on Lake Como every summer — this will be our fifth. On Harbour Island, we always rent a house close to our daughter Susanna’s house. We’re staying with great friends in Telluride for the film festival.Raison d’être: Elizabeth [Showers] has put the Harbour Island trip together. We’ll have the big birthday celebration at The Dunmore beach club. Como is so amazingly beautiful and is accessible to so many other places we love in Switzerland, so we use the villa as a base and do a lot of traveling the month we’re there.Posse: Family!First Things First: Get organized. I have to unpack, make sure the house looks the way I want it to look (usually with flowers everywhere). On Harbour Island, we’ll head to Sip Sip for lunch. On Lake Como, we will go down the hill from our villa and have the most delicious lunch on the water — northern Italian style.

Near The Ashram, Calabasas

Janet GridleyInterior designerDestination: I’m heading to the Santa Monica Mountains above Malibu for a weeklong retreat. It’s a hardcore, no-frills, tough-love boot camp. We’ll be hiking 10 miles every day, so let’s not call it a vacation. I’m actually quite scared.In Residence: The Ashram in Calabasas, California.Raison d’être: I grew up in Palos Verdes, climbing the goat trails to the ocean and getting really dirty. When I scramble down a dusty trail and smell the dry grasses and the Pacific, my head clears and I feel like a kid again. Isn’t there a cliché about saltwater being a cure for everything? There will definitely be sweating and possibly tears during the week, all within view of the Pacific, so I should emerge refreshed.Posse: My best freind since high school, Tara Poseley, is taking me for my birthday. She’s my inspiration and will know how to motivate me without coffee or wine.First Things First: I love a good West Coast sunset, preferably with a little fog. I plan on heading out to enjoy one of those straight away.

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Rome

Jessica JesseCo-founder, CEO and creative director, BuDhaGirlDestination: Off to Italy. Base camp will be Empoli, about 35 kilometers from Florence.Raison d’être: Italy has been on the check-off list for our daughter, Sloane. We will also be visiting Rome in this Jubilee year. St. Peter’s main door will be open — this is a big deal.In Residence: We are leasing a villa. Ten acres. Pool. Quiet.Posse: Well, let’s see, so far: Nancy Oakes and Bruce Aidells, Jean Michel Vallet, Rosita Rivas. Maybe Jan and Ka Yeung?First Things First: Provision. I set out to stock the villa with all our necessities: great soaps, butter, booze, wine and bread — all the rest can follow.

Alberto LombardiRestaurateur, Lombardi Family ConceptsDestination: We are celebrating my wife Vivian’s birthday with family in Italy.In Residence: When we visit the family, we stay in Hotel Aurelia in Milano Marittima, a terrific little town on the Adriatic coast.Raison d’être: My family lives nearby. We’ve been staying in this quaint hotel for years. It’s the perfect family destination.Posse: All of our children, with spouses, and seven grandchildren.First Things First: Hit the tennis courts. There is a fantastic clay-court tennis center within walking distance from the hotel.

Hôtel du Cap-Eden-Roc, Cannes

Cindy RachofskyCo-founder and host, TWO X TWO for AIDS and Art benefitting amfAR/Dallas Museum of Art
Destination: Cannes, Burgundy, Bordeaux, Zurich, Basel, Copenhagen, Berlin.In Residence: Hôtel du Cap-Eden-Roc in Cannes; Baur au Lac in Zurich; Hotel D’Angleterre in Copenhagen and Hotel du Rhome in Berlin.Posse: Alone to Cannes. Ann Colgin and Joe Wender, vintner friends from Napa, to Bordeaux and Burgundy. My art buddies to Basel and Zurich, where we eat baby chicken at the same restaurant every one of the four nights we are there. With a friend from L.A. (a fellow taco lover) to Copenhagen, and just the two of us to Berlin. (Trying to talk some Dallas friends into going — they know who they are!)Raison d’être: Cannes for amfAR gala; Burgundy and Bordeaux to drink wine (what else); Zurich and Basel for Basel Art Fair; Copenhagen to eat … tacos at Hija de Sanchez; Berlin for a friend’s wedding.First Things First: Eat!

The Imperial Spa, New Delhi

Tessa MugicaDirector of design, WisteriaDestination: I will first go to Spain to visit family: Madrid and San Sebastián — the most charming resort small town in Europe. Next will be a Wisteria work trip to India — New Delhi and Bombay.In Residence: In San Sebastián, I stay at Hotel Maria Cristina, open since 1912. We have many family memories in that hotel. In India, I will stay at The Imperial, which has the best spa in New Delhi. I love the 1930s atmosphere of the hotel.First Things First: The first thing I do when I arrive in Madrid is breakfast at Chocolatería San Ginés in the old town, where they’ve had the best hot cocoa and churros, open since 1894. The first thing I do when I arrive to San Sebastián is to make a promenade along the bay — the famous Paseo de la Concha, which literally means “promenade of the shell” because the bay has the shape of a scallop shell, with an island called Santa Clara in the middle, which has the shape of a turtle. Yes, it’s as magical as it sounds. Then I buy pastries at Barrenetxe. The first thing I will do in India is dinner at the charming veranda of The Imperial’s Italian Restaurant 1911. You can still feel the British colonial ambiance. I will go to this trip with Wisteria’s Parisian agent, Serge Milan, and we will navigate through antique markets and visit artisans looking for the best of the best in furniture and accessories making.

Christen WilsonArt collectorDestination: New York CityRaison d’être: Frieze Art Fair opens this month. I’m also co-chair of the Tate Artists Dinner on May 3, and need to get there a bit early for that … We are excited to have over 40 artists being honored and attending. We are also celebrating the opening of the new Tate Modern building in London at the dinner.In Residence: The New York Edition on Madison Avenue. My first time, so I will let you know how it goes.Posse: My husband, Derek Wilson.First Things First: When I arrive, the first thing I will do is check in and head straight to a party that Ken Fulk is having at his TriBeCa loft. NYC is crazy that week, because the Met Ball is also going on.